Design, synthesis, and evaluation of azapeptides as substrates and inhibitors for human rhinovirus 3C protease

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 4, 1999, Pages 577-580

  Venkatraman, Shankar ^a   Kong, Jian she ^a   Nimkar, Sanjay ^a   Wang, Q May ^b   Aubé, Jeffrey ^a   Hanzlik, Robert P ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZAPEPTIDE ESTER DERIVATIVE; BOC VLFAQ OPH; PROTEINASE INHIBITOR; RHINOVIRUS 3C PROTEASE; UNCLASSIFIED DRUG; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME METABOLISM; HYDROLYSIS; INHIBITION KINETICS; NONHUMAN; PEPTIDE ANALYSIS; RHINOVIRUS;

AZA COMPOUNDS; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; DRUG DESIGN; HYDROLYSIS; PEPTIDES; SUBSTRATE SPECIFICITY; VIRAL PROTEINS;

HUMAN RHINOVIRUS 3; HUMAN RHINOVIRUS SP.; RHINOVIRUS;

EID: 0033593862     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00049-9     Document Type: Article

References (19)

1. 1. Reviews: (a) Gorbalenya, A. E.; Snijder, E. J. In Cysteine Proteases: Evolution, Function, and Inhibitor Design; J. H. McKerrow, J.H.; James, M.N.G., Eds.; ESCOM Science: Leiden, 1996; pp 64-86.
2. (b) Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
3. 2. Skern, T.; Liebig, H.-D. Meth. Enzymol. 1994, 24, 583.
4. 3. Cheah, K.-C.; Leong, L. E.-C; Porter, A. G. J. Biol. Chem. 1990, 265, 7180.
5. 4. Kean, K. M.; Howell, M. T.; Grünert, S.; Girard, M.; Jackson, R. J. Virology 1993, 194, 360.
6. 5. Webber, S. E.; Okano, K.; Little, T. L.; Reich, S. H.; Xin, Y.; Fuhrman, S. A.; Matthews, D. A.; Love, R. A.; Hendrickson, T. F.; Patrick, A. K.; Meador III, J. W.; Ferre, R. A.; Brown, E. L.; Ford, C. E.; Binford, S. L.; Worland, S. T. J. Med. Chem. 1998, 41, 2786.
7. 6. Shepherd, T. A.; Cox, G. A.; McKinney, A.; Tang, J.; Wakulchik, M.; Zimmerman, R. E.; Villareal, E. C. Bioorg. Med. Chem. Lett. 1996, 6, 2893.
8. 7. Kaldor, S. W.; Hammond, M.; Dressman, B. A.; Labus, J. M.; Chadwell, F. W.; Kline, A. D.; Heinz, B. A. Bioorg. Med. Chem. Lett. 1995, 5, 2021.
9. 8. Webber, S. E.; Tikhe, J.; Worland, S. T.; Fuhrman, S. A.; Hendrickson, T. F.; Matthews, D. A.; Love, R. A.; Patick, A. K.; Meador, J. W.; Ferre, A. A.; Brown, E. L.; DeLisle, D. M.; Ford, C. E.; Binford, S. L. J. Med. Chem. 1996, 39, 5072.
10. 9. Jungheim, L. N.; Cohen, J. D.; Johnson, R. B.; Villareal, E. C.; Wakulchik, M.; Loncharich, R. J.; Wang, Q. M. Bioorg. Med. Chem. Lett. 1997, 7, 1589.
11. 10. Molla, A.; Hellen, C. U. T.; Wimmer, E. Journal of Virology 1993, 67, 4688.
12. 11. Sham, J. L.; Rosenbrook, W.; Kari, W.; Betebenner, D. A.; Wideburg, N. E.; Saldivar, A.; Plattner, J. J.; Norbeck, D. W. J. Chem. Soc. Perkin Trans. I 1995, 1081.
13. 12. Kong, J.-S.; Venkatraman, S.; Furness, K.; Nimkar, S.; Shepherd, T. A.; Wang, Q. M.; Aube, J.; Hanzlik, R. P. J. Med. Chem. 1998, 41, 2579.
14. 13. Dragovich, P. S.; Webber, S. E.; Babine, R. E.; Fuhrman, S. A.; Patrick, A. K.; Matthews, D. A.; Lee, C. A.; Reich, S. H.; Prins, T. J.; Marakovits, J. T.; Littlefield, E. S.; Zhou, R.; Tikhe, J.; Ford, C. E.; Wallace, M. B.; Meador III, J. W.; Ferre, R. A,; Brown, E. L.; Binford, S. L.; Harr, J. E. V.; DeLisle, D. M.; Worland, S. T. J. Med. Chem. 1998, 41, 2806.
15. 14. Dragovich, P. S.; Webber, S. E.; Babine, R. E.; Fuhrman, S. A.; Patrick, A. K.; Matthews, D. A.; Reich, S. H.; Marakovits, J. T.; Prins, T. J.; Zhou, R.; Tikhe, J.; Littlefield, E. S.; Bleckman, T. M.; Wallace, M. B.; Little, T. L.; Ford, C. E.; Meador III, J. W.; Ferre, R. A.; Brown, E. L.; Binford, S. L.; DeLisle, D. M.; Worland, S. T. J. Med. Chem. 1998, 41, 2819.
16. 15. Xing, R.; Hanzlik, R. P. J. Med. Chem. 1998, 41, 1344.
17. 16. Magrath, J.; Abeles, R. H. J. Med. Chem. 1992, 35, 4279.
18. 13CNMR, EI-MS, HR-FABMS spectra, and reverse-phase HPLC data.
19. 18. Birch, G. M.; Black, T.; Malcolm, S. K.; Lai, M. T.; Zimmerman, R. E.; Jaskunas, S. R. Prot. Expr. Purif. 1995, 6, 609.